Tupac Shakur Said 1 Frank Sinatra Song Was ‘Too Beautiful to Mess With’

Rappers are known for sampling other hits to make new songs. However, Tupac Shakur thought one of Frank Sinatra’s most famous songs was so perfect he didn’t want to mess with it. Here’s a look at the story behind a Tupac version of a Sinatra song that never was — and a look at whether Sinatra was more popular on the charts than Tupac.

Tupac Shakur in a bandana next to Frank Sinatra in a fedora
Tupac Shakur and Frank Sinatra | (L): Raymond Boyd/Getty Images, (R): GAB Archive/Redferns

How Tupac Shakur became interested in Frank Sinatra songs

Sinatra’s “Fly Me to the Moon” is one of the most famous songs of his career. The track was not a hit on the Billboard Hot 100 because it was not released as a single. However, his cover of the track became heavily associated with the Apollo Space Program and it has been featured in a number of films like Clint Eastwood’s Space Cowboys.

Even many years after the song became famous, Jim Belushi was listening to it. Belushi told TMZ he got Tupac Shakur interested in Sinatra while they were working on the film Gang Related. Belushi revealed the rapper had a soft spot for love songs. 

“Fly Me to the Moon”

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“We had a connection that went beyond words,” Belushi told Vibe. “It’s just a chemistry, a nonverbal jam. And we jammed throughout that whole movie. I had a ball with him. We were trying to do a rap version of ‘Fly Me to the Moon..’ He didn’t really know [Frank] Sinatra’s work. And we’d sit in his trailer and listen to it. He was so blown away by the melodic nature of Frank’s voice. We toyed with it for a week or two and he said, ‘That song, the way Frank Sinatra does it is just too beautiful to mess with.’”

Why Marlon Wayans thought Tupac Shakur was like Frank Sinatra

Interestingly, Marlon Wayans, an actor who worked with Tupac on the film Above the Rim, compared the rapper to Sinatra. “‘Pac was eventually going to win some Academy Award,” he opined. “He was like a Frank Sinatra. He was that powerful. There was no ceiling.”

“California Love”

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This raises an interesting question: Which artist was more popular: Sinatra or Tupac? Sinatra released singles that reached the Billboard Hot 100. Of these singles, three reached the top 10, specifically “That’s Life,” “Strangers in the Night,” and “Somethin’ Stupid.” The latter two singles reached the top of the chart. Notably, Sinatra’s career started years before the Billboard Hot 100 began, so he had hits which are not represented by the chart.

“Somethin’ Stupid”

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On the other hand, Tupac released singles that charted on the Billboard Hot 100. Of these singles, two reached the top 10: “Dear Mama/Old School” and “California Love.” The latter reached No. 1 on the chart. Regardless of who was more popular, Tupac clearly appreciated Sinatra’s art.

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